3-(2-Morpholin-4-ylethoxy)benzaldehyde → 5-iodo-N-[(E)-[3-(2-morpholin-4-ylethoxy)phenyl]methylideneamino]pyridin-2-amine

HRID 1041900Notes

Reaction equation

HRID 1041900 reaction equation
[I:1][C:2]1[CH:3]=[CH:4][C:5]([NH:8][NH2:9])=[N:6][CH:7]=1.[N:10]1([CH2:16][CH2:17][O:18][C:19]2[CH:20]=[C:21]([CH:24]=[CH:25][CH:26]=2)[CH:22]=O)[CH2:15][CH2:14][O:13][CH2:12][CH2:11]1>CCO>[I:1][C:2]1[CH:3]=[CH:4][C:5]([NH:8]/[N:9]=[CH:22]/[C:21]2[CH:24]=[CH:25][CH:26]=[C:19]([O:18][CH2:17][CH2:16][N:10]3[CH2:15][CH2:14][O:13][CH2:12][CH2:11]3)[CH:20]=2)=[N:6][CH:7]=1

Participants

4

Reactant 2

HCID 71646203-(2-Morpholin-4-ylethoxy)benzaldehydeHCID 223971882-Hydrazinyl-5-iodopyridine

Product 1

HCID 872226535-iodo-N-[(E)-[3-(2-morpholin-4-ylethoxy)phenyl]methylideneamino]pyridin-2-amineYield 86,306.898%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a suspension of 5-iodo-2-hydrazinopyridine (6.62 g, 0.028 mmol) in EtOH (90 mL) was added 3-(2-morpholin-4-yl-ethoxy)-benzaldehyde (6.63 g, 0.028 mmol). The reaction was heated at reflux for 2 h under nitrogen, then cooled to RT. The resulting precipitate was collected by filtration and washed with EtOH to afford the title compound (10.93 g, 86%) as a white solid. LCMS (Method 1): Rt 2.37 min, m/z 453 [MH+]. 1H NMR (300 MHz, CD3OD): δ 8.24 (1 H, d, J 2.2), 7.90-7.84 (2 H, m), 7.36-7.18 (3 H, m), 7.12 (1 H, d, J 8.8), 6.94-6.89 (1 H, m), 4.19 (2 H, t, J 5.4), 3.72 (4 H, t, J 4.6), 2.83 (2 H, t, J 5.4), 2.62 (4 H, t, J 4.6).

Workup

  1. temperatureThe reaction was heated
  2. temperatureat reflux for 2 h under nitrogen
  3. filtrationThe resulting precipitate was collected by filtration
  4. washwashed with EtOH

Sources & evidence

ORD record
ord-36d1839aca73495f853ddba1ecaaba51
Source dataset
uspto-grants-2013_10
Patent number
US08557797B2

Reaction notes

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